Metal salts of 12-ketostearic acid



Patented Sept. 24, 1940 UNITED STATES- PATENT, OFFICE 2,215,955 METALSALTS F IZ-KETOSTEARIC ACID Henry L. Cox, SouthCharleston, W. Va.,assignor, by mesne assignments, to Union Carbide and Carbon Corporation,York a corporation of New NoDrawing. Original application June 7, 1934,

Serial No. 729,442. Divided and this application April 7, 1939, SerialN0. 266,707

. 3 Claims.

The invention relates to new chemical compounds, in particular metalsalts of 12-ketostearic acid.

The scope of the invention, and thenew chemi- 5 cal compounds includedtherein, may be represented by the following structural formula:

[CHE-(CH2) 5CO-(CH2) 1o-COO] 12R in which R is a metallic elementindicative of salts of this acid, and n is one or more depending uponthe valency of R. These salts are solid waxy materials at atmospherictemperatures, and the compounds exhibit properties especially desirableas stabilizers and plasticizers in lacquer 15 and plastic compositionsformulated from natural and synthetic gums and resins.

The 12-ketostearic acid may be prepared by oxidizing 12-hydroxy-stearicacid,

CH3 (CI-I sCI-I (OH) (CH2) mCOOI-I which in turn can be synthesized fromcastor oil. Castor oil consists chiefly of the glyceride of ricinoleicacid, or triricinolein, which when hydrogenated, saponified with sodiumhydroxide, and

then hydrolyzed with acid, will yield the above hydroxystearic acid. Byfurther treatment of this acid with chromic acid, or other oxidizingagent, a carbonyl group is formed at the 12 position of the molecule,and the resulting product is 1'2- 0 ketostearic acid. The carboxylhydrogen of the acid can be replaced with a metal by reacting the acidwith sodium hydroxide to produce sodium -12- ketostearate, and treatingthe latter with a salt of the metal desired.

As illustrative of the manner of preparing the 12-ketostearic acid, andcertain of its salts, the following examples are given:

Example 1 I Castor oil was treated in the manner previously indicated,and a quantity of l2-hydroxystearic acid was obtained and identified byits known properties. One hundred and fifty grams of this hydroxystearicacid was dissolved in 250 grams of acetic acid. With constant stirring amixture of grams of chromic acid (CIOs) m 500 grams of acetic acid wasgradually added at a temperature of 30 to C. After the reaction wascomplete,

the whole was poured into several volumes of water, and a crude productcrystallized out. This was dissolved in methanol, again precipitatedwith water, and then dried. A final yield of 120 grams was obtained,which had an acetyl number of substantially zero, and an equivalentweight and other properties indicating the product 12- ketostearic acid,which may structural formula In substantially the same manner as Example2, a sodium soap of 12-ketostearic acid was made, and to this calciumacetate was added. The product precipitating out on dilution with water,was washed, dried, and identified as calcium 12- ketostearate. This wasa White waxy solid melting at 138to 140 C., and having the probablestructural formula [GHQ-(CH2) 5CO(CH2) 10-000] 2Ca The invention shouldnot be limited other than as defined inthe. appended claims. Thisapplication is a division of my copending application Serial No.729,442, filedJune '7, 1934.

I claim: i

1. A metal salt of l2-ketostearic acid.

2. Calcium lz-ketostearate.

3. Copper 12,-,ketostearate.

HENRY L. COX.

be represented by the

